US11814347B2ActiveUtilityA1

Method for producing fluorinated compounds

72
Assignee: MERCK PATENT GMBHPriority: Sep 26, 2017Filed: Dec 16, 2021Granted: Nov 14, 2023
Est. expirySep 26, 2037(~11.2 yrs left)· nominal 20-yr term from priority
C07C 41/14C07C 17/2637C07C 17/272C07C 41/03C07C 43/137C07D 303/24C09D 5/006C09D 7/40C09D 7/61
72
PatentIndex Score
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Cited by
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References
16
Claims

Abstract

The present invention relates to a process for the preparation of fluorinated compounds, to novel compounds containing fluorinated end groups, to the use thereof and to compositions comprising novel compounds containing fluorinated end groups.

Claims

exact text as granted — not AI-modified
The invention claimed is: 
     
       1. A compound of formula (I′) 
       
         
           
           
               
               
           
         
         where 
         Rf is CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —, 
         a=1 or 2, 
         b=1, 
         c=0, 
         d=0, 
         R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′, 
         Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, 
         and, if R is a group Rf′, Rf and Rf′ are different, 
       
       or 
       of formula (VI′) 
       
         
           
           
               
               
           
         
         where 
         Rf is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, 
         L is a single bond or a divalent organic group, and 
         X is a cationic, amphoteric or anionic group. 
       
     
     
       2. A compound of formula (I′) 
       
         
           
           
               
               
           
         
         where 
         Rf is CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —, 
         a=1 or 2, 
         b=1, 
         c=0, 
         d=0, 
         R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′, 
         Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, 
         and, if R is a group Rf′, Rf and Rf′ are different. 
       
     
     
       3. The compound according to  claim 2 , wherein Rf is CF 3 —(CF 2 )—O—. 
     
     
       4. The compound according to  claim 2 , wherein R is a C1-C20 alkyl group. 
     
     
       5. The compound according to  claim 2 , wherein Rf′ is of the following formula
   CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —(CR 1 R 2 ) e —(CR 3 R 4 ) f —O g —,
 
 where 
 R 1 , R 2 , R 3  and R 4 , independently of one another, are hydrogen or an alkyl group, 
 a=0, 1, 2 or 3, 
 b=0 or 1, 
 c=0, 1, 2 or 3, 
 d=0 or 1, 
 e=0, 1, 2, 3 or 4, 
 f=0, 1, 2, 3 or 4 and 
 g=0 or 1. 
 
     
     
       6. The compound according to  claim 2 , wherein Rf is CF 3 —(CF 2 ) 2 —O—. 
     
     
       7. The compound according to  claim 1 , which is a compound of formula (VI′). 
     
     
       8. The compound according to  claim 4 , wherein Rf is CF 3 —(CF 2 ) 0-3 — or CF 3 —(CF 2 ) 0-3 —O—. 
     
     
       9. The compound according to  claim 7 , wherein R is a C1-C20 alkyl group. 
     
     
       10. The compound according to  claim 7 , which is a compound of formula (VI′), wherein Rf is CF 3 —(CF 2 ) 0-3 —O—. 
     
     
       11. A product selected from the group consisting of paints, coatings, printing inks, protective coatings, special coatings in electronic or optical applications, photoresists, top antireflective coatings or bottom antireflective coatings, developer solutions and wash solutions and photoresists for photolithographic processes, cosmetic products, agrochemicals, floor polishes, photographic coatings and coatings of optical elements, comprising a compound according to  claim 7 . 
     
     
       12. A composition comprising one or more compounds according to  claim 7  and a vehicle which is suitable for an application. 
     
     
       13. The composition according to  claim 12 , which is selected from the group consisting of paints, coating preparations, fire-extinguishing compositions, lubricants, washing compositions, cleaning compositions, de-icers, developer solutions, wash solutions, photoresists for photolithographic processes, cosmetic products, agrochemicals, floor polishes, hydrophobicising compositions for textile finishing and hydrophobicising compositions for glass treatment. 
     
     
       14. A compound of formula (VI′) 
       
         
           
           
               
               
           
         
         wherein 
         Rf′ is of the following formula
   CF 3 —(CF 2 ) a —O b —(CF 2 ) c —O d —(CR 1 R 2 ) e —(CR 3 R 4 ) f —O g —,
 
 
         where 
         R 1 , R 2 , R 3  and R 4 , independently of one another, are hydrogen or an alkyl group, 
         a=0, 1, 2 or 3, 
         b=0 or 1, 
         c=0, 1, 2 or 3, 
         d=0 or 1, 
         e=0, 1, 2, 3 or 4, 
         f=0, 1, 2, 3 or 4, and 
         g=0 or 1, 
         R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′, 
         Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, 
         L is a single bond or a divalent organic group, and 
         X is a cationic, non-ionic, amphoteric or anionic group, 
         and, if R is a group Rf′, Rf and Rf′ are different. 
       
     
     
       15. A compound of formula (VI′) 
       
         
           
           
               
               
           
         
         wherein 
         Rf is CF 3 —(CF 2 ) 0-3 —, 
         R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′, 
         Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, 
         L is a single bond or a divalent organic group and 
         X is a cationic, non-ionic, amphoteric or anionic group 
         and, if R is a group Rf′, Rf and Rf′ are different. 
       
     
     
       16. A method for preparing a compound of formula (VI) 
       
         
           
           
               
               
           
         
         where 
         Rf is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, 
         R is a linear or branched alkyl group, optionally containing one or more heteroatoms, or a group Rf′, 
         Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, 
         L is a single bond or a divalent organic group and 
         X is a cationic, non-ionic, amphoteric or anionic group, 
         comprising 
         reacting a compound of formula (I) 
       
       
         
           
           
               
               
           
         
         where 
         Rf is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms, 
         R is a linear or branched alkyl or siloxane group, optionally containing one or more heteroatoms, or a group Rf′, and 
         Rf′ is a fluorinated, linear or branched alkyl group, optionally containing one or more heteroatoms.

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